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Forum Home > Oblivious To Love...or lack there of. > Alright, out with them: Worst Online Date Experience(s)

Michael J. Sielaff
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Posts: 1


I'll get the ball of my worst online dates- not a date online but a date with someone I met understand: 


So there was this physically attractive Indian woman on who, although didn't volunteer a lot of information in her profile, matched up with me on what she did put down: loves kids, passion for helping others, played tennis- and she had a fantastic smile.  Sold.  I messaged her and she responded.  The most difficult part was out of the way: getting a response.  After a few short messages, we exchanged phone numbers (finally someone who wasn't scared off by a simple request to meet up!  I mean, if you're on a dating website, why would you be chatting with a guy you wouldn't want to meet up with?  Tell me that, online daters who abruptly cut off communication!  Stop teasing!)  I gave her a call on a weekday evening, left a voice mail, and hoped for the best.  The next day- just before 7am- my phone rang.  Stupid telemarketers!  Just because I have a Minnesota area code, doesn't mean I live in Minnesota.  "Hello?"  "Is this Michael?"  "Yes."  No response.  I checked the caller ID.  It was the Indian chick!  "Oh, hi- is this Amy?"  "Yes."  "Great- how are you?"  "Good."  "I'm glad we connected.  I called because..."  To this day, I'm not sure how she did it, but she reversed the conversation on me.  I felt like I had called her.  By this time, I recognized this wasn't the conclusion to my dream about breeding narwhals.  Shaking off my slumber, I realized I had to take charge.  "So, you can you meet up on Thursday at 7?"  As she nervously whispered "Yes," it was official- our first date was set.  


I told her I'd pick out a restaurant in her neck of the woods since she had no preference (surprise!) and would text her the details.  Now, picking out a first date restaurant is always tricky- not too fancy (in case it's too much, too soon or if we don't end up going Dutch), but not too casual (why isn't Denny's officially considered a fast food joint yet?  I mean, they're cheaper than Jimmy's hot dog cart up the street).  And because my date is Indian-American, I figured I shouldn't choose anything ethnic out of fear that she would assume that I assumed she only likes non-white cuisine.  Is that white guilt or racism?  Anyway, I settled on a high-rated on Yelp, medium-cost, Italian place.  I texted her the address and told her it was a "nice casual" restaurant.  Whew.  Now I just had to show up on time, have an engaging conversation, not talk too much, not talk too little, be funny, be interesting, and pick up on non-verbal signals.  Piece of Italian Cream Cake.  


On my way to Maria's Italian Kitchen, I found myself caught in much more traffic then anticipated.  Great start, huh?  I called, letting her know I was running no more than 10 minutes late.  "Okay, thanks for letting me know.  Drive safe."  Sounded like she understood AND wasn't angry.  Good deal.  Because realistically she's was going to have to get used to this whole late thing if we were ever going to work.  Five minutes later, she calls: "Are you almost here?"  "Yes, I'm about five minutes away.  Sorry!"  My E.T.A. hadn't changed if that's what she was asking.  Two minutes later, she called again.  "Where are you?"  "I'm just exiting, I should be there in two minutes.  Thanks for waiting!"  Come, on Amy.  Trust me.  Or at least remember that I JUST spoke with you on the phone a YouTube video ago.  I'm not ditching you!  I parked, spit out my gum, checked my comb-over in the mirror (it's really a side-part, but I've always referred to it as a comb-over...but these days, it's actually starting become a comb-over- unfortunately your Christmas gift of prescription-strength hair thickening shampoo didn't work, Mom), took a deep breath: it's Go Time.  I walked up to the restaurant, looking for a pretty Indian women.  Bam!  There she was.  Even prettier than her profile pictures.  This never happens.  What a pleasant surprise.  But she clearly didn't take my advice.  I was nice casual, she was completely dressed up- I mean, this wasn't a wedding.  "Amy?"  "Hi."  "I'm so sorry I'm late."  "That's fine, not a big deal at all.  I was a little late myself."  What?  Then why did you call me twice after I said- STOP, Michael.  Now is not the time.  Don't mentally shoot yourself in the foot before this thing even starts.  "Okay, great.  Shall we?"  Let the date begin!



We journeyed into the restaurant together. Huh. The place was even more casual then advertised. I felt like I was in the Denny's version of Olive Garden (Yep, another Denny's reference- who knew it would be such a good descriptor?).  Amy would have been over-dressed either way, but now I was even feeling like I shouldn't have worn khakis and polo (not that I have anything else in my wardrobe, mind you). We sat down, took a look at the menu, ordered, and the conversation began. Or at least me talking did. I asked her questions. She responded with one word answers. I made jokes. They went completely over her head. And I suppose I made the mistake of sitting by the window because every time she spoke, she looked out the window like she was internally searching for reasons why she agreed to go on this date. After the meal, she excused herself to the restroom and I thought about taking bets with the Latino waiter if she'd come back. Wow. This was not going well. At least the ravioli made a good first impression. It had just the right amount of cheese. Hey- I'm not blameless here, either- if Amy was uninterested and couldn't hold a conversation, I was talking too much about myself and trying too hard to be funny. Although, she did respond to a joke I made with a monotone “That' funny.”  That's something.



I checked my fictional watch. It had been 10 minutes and she still wasn't back from the lavatory. I should have taken that bet with the waiter. I asked for more bread. Was she throwing up the food she just ate?  Was she a slow pooper?  Should I go in there and save her from her eating disorder? At the 15 minute mark she finally came back. The check was on the table. To amuse myself, I asked if she wanted to go bowling. “I haven't bowled in a while. But I don't think I want to. I'm not dressed for it.” No kidding. “Want to go to a bar and grab a drink?” Ah, what? She wanted to continue this disastrous date? “Okay. I don't really know this area, do you have any suggestions?” “Yeah, I know of a really good place up the street.” “Great. Want to carpool?” “How about you follow me there?” “Sure.” The bill laid dormant. Not even a reach. All I want is a reach. But I never said anything before dinner and I didn't want to make her feel awkward so I paid for her meal. I'm a reluctant gentleman. Or have ancestors from the Netherlands.


So, I followed her Mercedes to this recommended bar. This will be interesting, I thought. And it was. As soon as I started following her. She drove like she was in a getaway vehicle- weaving in and out of traffic. Come on, I have no idea where you're going, at least use your blinker! We started getting a little further away from the downtown area of the city. I wondered if she forgot I was following her or wised up and decided to go home. She sped into a mall parking lot. Is she turning around? I don't see any bars around here, I only see a Chili's...and that's exactly where she was going. Chili's. The hottest bar this side of suburbia. Maybe we could get some Baby Back Ribs for dessert. We walked in, briefly sat at the novelty bar reserved for making the place look like an All-American, working-man's pub. “Can we sit in a booth instead?” Sure. We sat at a table for dinner, so let's mix it up. “What are you ordering?” She was becoming more talkative which was good. “I don't usually drink much, so recommend me a drink you like.” “Oh, you don't drink? I'm sorry. You don't have to order alcohol.” “No, no. I don't drink that often so I don't really know what I like.” “Oh, it's not a big deal, I didn't know you don't drink.” She wasn't getting it. And now felt embarrassed. Note to self: just order a drink and save honestly for the second date. She pressured me so much NOT to get an alcoholic beverage, I said, screw it. “I'll have a Raspberry Lemonade.” “And I'll have red wine.” So we sat there. With a red wine and raspberry lemonade. At Chili's. Talking. After finishing her drink, she excused herself to the restroom. I timed her this time.


11 minutes, 25 seconds. Was she throwing up her red wine? “I have to work tomorrow, so I'm going to have to get going.” “No problem.” The waiter brought the check. She'll reach for this one, right? Nope. Fortunately the waiter forgot to put the lemonade on the check, so I felt a little redemption. As we left Chili's, we said our goodbyes. “Great meeting you, Amy. I had a good time.” “Yeah, so did I. I'm cold. Drive safe.” Apt. Wow. I am glad that was over. 10 minutes later she texted me. Why? To say she had a “gr8 time ” Strange. I drove home thinking I'll never hear from her again. Or want to. Unless I'm shopping for more awkward dating stories...the next morning, what do I awake to? A text that reads: “Good morning, have a nice day.” Did we go on the same date last night? Did I have one too many raspberry lemonades? Did we end up going back to her place to have even more uncomfortable interaction in the form of nude body contact? I think I would have remembered that. I decided not to respond until I knew what to say. Six hours later, she sends me another text: “Hope you're having a nice day.” Repetitive but sweet. I had to break this off ASAP. So I texted her: “I hope you're having a nice day too! I had a good time yesterday too and think you're great. But I don't feel we had a lot of romantic chemistry and therefore think we shouldn't go on another date. If you want to hang out as friends, though, I'd be down. You deserve a great guy!” Her reply? “Ok!” She wasn't as attached as I assumed. I mean, we were definitely not on the same page, let alone the same that I think about it, I don't think we were even in the same library.

June 13, 2013 at 7:17 PM Flag Quote & Reply

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